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Saccharide-functionalized alkanethiols for fouling-resistant self-assembled monolayers: Synthesis, monolayer properties and anti-fouling behaviour
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Professor Tony Clare
Fyrner T, Lee H-H, Mangone A, Ekblad T, Petitt M, Callow M, Callow J, Conlan S, Mutton R, Clare AS, Konradsson P, Liedberg B, Ederth T
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We describe the synthesis of a series of mono-, di- and trisaccharide-functionalized alkanethiols, as well as the formation of fouling-resistant self-assembled monolayers (SAMs) from these. The SAMs were characterized using ellipsometry, wetting measurements, and infrared reflection-absorption spectroscopy (IRAS). We show that the structure of the carbohydrate moiety affects the packing density and that this also alters the alkane chain organization. Upon increasing the size of the sugar moieties (from mono- to di- and tri-saccharides), the structural qualities of the monolayers deteriorated, with increasing disorder, and for the trisaccharide, a slow reorganization dynamics in response to changes in environment polarity was observed. The anti-fouling properties of these SAMs were investigated through protein adsorption experiments from buffer solutions, as well as settlement (attachment) tests using two common marine fouling species, zoospores of the green macroalga <i>Ulva linza</i> and cypris larvae of the barnacle <i>Balanus amphitrite</i>. The SAMs show overall good resistance to fouling by both the proteins and the tested marine organisms. In order to improve the packing density of the SAMs with bulky head-groups, we employed mixed SAMs, where the saccharide-thiols are diluted with a filler molecule having a small 2-hydroxyethyl headgroup. This method also provides a means by which the steric availability of sugar moieties can be varied, which is of interest for specific interaction studies with surface-bound sugars. The results of the surface dilution study and the low non-specific adsorption onto the SAMs both indicate the feasibility of this approach.
American Chemical Society
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